EP0309541A1 - Sulfonyle carboxamides. - Google Patents

Sulfonyle carboxamides.

Info

Publication number
EP0309541A1
EP0309541A1 EP88903531A EP88903531A EP0309541A1 EP 0309541 A1 EP0309541 A1 EP 0309541A1 EP 88903531 A EP88903531 A EP 88903531A EP 88903531 A EP88903531 A EP 88903531A EP 0309541 A1 EP0309541 A1 EP 0309541A1
Authority
EP
European Patent Office
Prior art keywords
compound
formula
give
reacting
pharmaceutically acceptable
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP88903531A
Other languages
German (de)
English (en)
Other versions
EP0309541A4 (fr
EP0309541B1 (fr
Inventor
Anthony F Kreft Iii
John H Musser
Dennis M Kubrak
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Wyeth LLC
Original Assignee
American Home Products Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by American Home Products Corp filed Critical American Home Products Corp
Publication of EP0309541A1 publication Critical patent/EP0309541A1/fr
Publication of EP0309541A4 publication Critical patent/EP0309541A4/fr
Application granted granted Critical
Publication of EP0309541B1 publication Critical patent/EP0309541B1/fr
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/47—Quinolines; Isoquinolines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D215/14—Radicals substituted by oxygen atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/08—Antiallergic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

Definitions

  • Compounds of formula (XVb) may be prepared by reducing (eg. using NaBH 4 ) a corresponding ketone of formula CXIIIa) and halogenating the alcohol product using, for example, SOCl 2 .
  • Example 4 The compounds 5- and 12-hydroxyelcosatetraenoic acid (5-HETE and 12- HETE) and 5,12-dihydroxyeicosatetraenoic acid (5.12-d ⁇ HETE) are early arachidonic acid oxidation products in the lipoxygenase cascade, which have been shown to mediate several aspects of inflammatory and allergic response.
  • the assay of this Example measures the ability of the compounds of the invention to inhibit the synthesis of 5-HETE by rat glycogen elicited polymorphonuclear leukocytes.
  • the assay is carried out as follows: Peritoneal PMN are obtained from female Wistar rats (150-250 g) that received an i.p. injection of 6% glycogen (10 ml).
  • Example 3 when tested in this assay, exhibited an IC 50 value of 6 ⁇ M, evidencing a significant activity in inhibiting the synthesis of th e arachidonic acid lipoxygenase oxidation product 5-HETE.
  • mice Male Hartley strain guinea pigs (350-600g) are anesthetized with pentobarbital sodium (50 mg/kg, i.p.).
  • the jugular vein is cannulated for injection of drugs and the carotid artery for monitoring blood pressure.
  • the trachea is cannulated for artificial ventilation by a miniature Starling pump and for indirect measurement of respiratory volume changes.
  • the animals are then pretreated with succinylcholine (2 mg/kg i.v.) and indomethacin (10 mg/kg i.v. in trizma 8.3 buffer, 9 minutes prior to leukotriene challenge).
  • Submaxirnal bronchoconstrictor responses are established in control animals by varying the dose-levels of leukotriene.

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Epidemiology (AREA)
  • Immunology (AREA)
  • Pain & Pain Management (AREA)
  • Rheumatology (AREA)
  • Pulmonology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Polyamides (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
  • Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Seasonings (AREA)
  • Peptides Or Proteins (AREA)

Abstract

Composés de formule (I) dans laquelle W est -O-, -S-, alpha ou -CH2-; X est O, S, NR2, CH=CH, CH=N ou N=CH; Y est -CH2O-, -CH2S-, beta, -O-, -S-, psi, delta, epsilon ou phi; R1 est un alkyle inférieur, un perfluoralkyle inférieur ou phényl substitué avec R5; R2 est l'hydrogène ou un alkyle inférieur; R3, R4 et R5 sont, indépendamment l'hydrogène, un alkyle inférieur, un nitro, un trifluorométhyle, un holo, un alcoxy inférieur, un alcoxycarbonyle inférieur ou un alcanoyloxy inférieur; n est égal à 0 ou 1; m a une valeur de 0 à 10 sont également décrits les sels pharmaceutiques de cette substance, et leur utilisation dans le traitement des obstructions des voies respiratoires nasales bronchiales induites par le leucotriène, telles que la rhinite allergique, l'asthme allergique bronchiale et les troubles similaires, le psoriasis, la colite ulcérante, l'arthrite rhumatoïde ainsi que d'autres réactions d'hypersensibilité immédiates.
EP88903531A 1987-03-18 1988-03-16 Sulfonyle carboxamides Expired - Lifetime EP0309541B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US2745287A 1987-03-18 1987-03-18
US27452 1998-02-21

Publications (3)

Publication Number Publication Date
EP0309541A1 true EP0309541A1 (fr) 1989-04-05
EP0309541A4 EP0309541A4 (fr) 1989-07-24
EP0309541B1 EP0309541B1 (fr) 1992-01-02

Family

ID=21837822

Family Applications (1)

Application Number Title Priority Date Filing Date
EP88903531A Expired - Lifetime EP0309541B1 (fr) 1987-03-18 1988-03-16 Sulfonyle carboxamides

Country Status (9)

Country Link
EP (1) EP0309541B1 (fr)
JP (1) JPH01502755A (fr)
KR (1) KR890700345A (fr)
AT (1) ATE70976T1 (fr)
AU (1) AU1549788A (fr)
CA (1) CA1314048C (fr)
DE (1) DE3867401D1 (fr)
GB (1) GB2202223B (fr)
WO (1) WO1988006886A1 (fr)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3908298A1 (de) * 1989-03-14 1990-09-20 Bayer Ag Substituierte (chinolin-2-yl-methoxy)phenyl-n,n'-sulfonylharnstoffe, verfahren zu ihrer herstellung und ihre verwendung in arzneimitteln
DE3916663A1 (de) * 1989-05-23 1990-11-29 Bayer Ag Substituierte (chinolin-2-yl-methoxy)phenyl-acyl-sulfonamide und -cyanamide, verfahren zu ihrer herstellung und ihre verwendung in arzneimitteln
DE3927369A1 (de) * 1989-08-19 1991-02-21 Bayer Ag Substituierte n-(chinolin-2-yl-methoxy)benzyl-sulfonyl-harnstoffe
DE3935139A1 (de) * 1989-10-21 1991-04-25 Bayer Ag Substituierte (chinolin-2-yl-methoxy)phenyl-thioharnstoffe
DE3935491A1 (de) * 1989-10-25 1991-05-02 Bayer Ag Substituierte (chinolin-2-yl-methoxy)phenyl-carbonylharnstoffe
US5021576A (en) * 1989-10-27 1991-06-04 American Home Products Corporation 2-Anilino phenylacetic acid derivatives
US5308850A (en) * 1991-09-30 1994-05-03 Merck Frosst Canada, Inc. (Bicyclic-hetero-arylmethoxy)indoles as inhibitors of leukotriene biosynthesis
EP0562796A1 (fr) * 1992-03-23 1993-09-29 Terumo Kabushiki Kaisha Composés d'acides phénoxyacétiques et compositions médicinales les contenant
CA2099188C (fr) * 1992-07-24 2005-12-13 Paul A. Bowser Utilisation d'une composition cosmetique
AU5686794A (en) * 1992-12-15 1994-07-04 Du Pont Merck Pharmaceutical Company, The (2-quinoxalinyloxy)phenoxypropanoic acids and related derivatives as anticancer agents
WO2005030206A1 (fr) * 2003-09-24 2005-04-07 Imclone Systems Incorporated Derives d'aryl-1,3-azole et procedes permettant d'inhiber l'activite de l'heparanase
CA2669704A1 (fr) * 2006-11-16 2008-05-22 Allergan, Inc. Sulfoximines en tant qu'inhibiteurs de la kinase

Family Cites Families (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3366630A (en) * 1963-10-26 1968-01-30 Hoechst Ag 2-(4'-amidostyryl)-benzoxazoles and method for using the same for the optical brightening of textiles
NZ193011A (en) * 1979-03-19 1983-03-15 Ici Australia Ltd Diarylamine derivatives intermediates herbicidal compositions
AU541697B2 (en) * 1979-11-19 1985-01-17 Ici Australia Limited Quinoline derivatives
CA1317299C (fr) * 1980-06-23 1993-05-04 Maged Mohamed Fawzi Ethers de type quinoxalinyloxy utilises comme agents selectifs de desherbage
US4594425A (en) * 1984-02-09 1986-06-10 American Home Products Corporation Heterocyclic compounds as antiallergic agents
US4675405A (en) * 1984-09-21 1987-06-23 American Home Products Corporation Quinoline compounds as antiallergic and antithrombotic agents
US4581457A (en) * 1984-09-21 1986-04-08 American Home Products Corporation Heterocyclic sulfonamides
NO174506B (no) * 1984-10-30 1994-02-07 Usv Pharma Corp Analogifremgangsmaate ved fremstilling av terapeutisk aktive forbindelser
EP0194599A3 (fr) * 1985-03-14 1988-01-20 Nissan Chemical Industries Ltd. Dérivés de benzamide, leur procédé de préparation et fongicides pour le sol les contenant
US4839369A (en) * 1985-04-16 1989-06-13 Rorer Pharmaceutical Corporation Aryl and heteroaryl ethers as agents for the treatment of hypersensitive ailments
US4631287A (en) * 1985-04-16 1986-12-23 Usv Pharmaceutical Corp. Aryl and heteroaryl ethers as agents for the treatment of hypersensitive ailments
DK282986A (da) * 1985-06-18 1987-02-24 Merck Frosst Canada Inc Substitueret quinolin og farmaceutisk praeparat indeholdende en saadan forbindelse
US4754043A (en) * 1985-10-03 1988-06-28 American Home Products Corporation Oxazole and thiazole naphthalenes as antiallergic agents
ATE68789T1 (de) * 1985-10-16 1991-11-15 Merck Frosst Canada Inc 2-substituierte chinoline.
US4684394A (en) * 1985-10-29 1987-08-04 The Dow Chemical Company Herbicidal aryloxyphenoxyalkanoate and alkenoate derivatives, compositions, and method of use therefor
DE3783951T2 (de) * 1986-05-30 1993-06-03 Ici Plc Heterozyklische verbindungen.

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO8806886A1 *

Also Published As

Publication number Publication date
GB2202223B (en) 1991-05-29
KR890700345A (ko) 1989-04-24
DE3867401D1 (de) 1992-02-13
WO1988006886A1 (fr) 1988-09-22
EP0309541A4 (fr) 1989-07-24
EP0309541B1 (fr) 1992-01-02
JPH01502755A (ja) 1989-09-21
CA1314048C (fr) 1993-03-02
GB2202223A (en) 1988-09-21
ATE70976T1 (de) 1992-01-15
GB8806373D0 (en) 1988-04-13
AU1549788A (en) 1988-10-10

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